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$278+ Cheap flights from New Windsor to Portland (SWF - PDX)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/20. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PDX
Apr 2 — Apr 91
Thu 4/2
Thu 4/9
1 adult, Economy
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Cheap flight deals from Stewart to Portland

One-way flights from Stewart to Portland
Search for one-way flight options from Stewart to Portland. Find affordable one-way fares based on user searches. Data last updated March 3, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/206:45 pm
SWF
-
PDX
2 stops22h 03m
Allegiant Air
Deal found 3/2$278
This Kiwi.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/112:05 pm
SWF
-
PDX
3 stops28h 53m
Multiple Airlines
Deal found 2/26$280
This Kiwi.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:46 pm
SWF
-
PDX
2 stops22h 21m
Allegiant Air
Deal found 2/26$303
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/276:45 pm
SWF
-
PDX
2 stops22h 03m
Allegiant Air
Deal found 3/2$344

Find flight deals from Stewart to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Portland (PDX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated March 3, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Popular in

December

Cheapest in

April

Average price

$387
Provider with most accurate pricing for New Windsor Stewart-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Portland flights.
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 3, 2026.
Use the filters below to find and compare flights from New Windsor to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Sat 6/20

6:45 pm-1:48 pm

2 stops22h 03m

$278

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Wed 7/1

12:05 pm-1:58 pm

3 stops28h 53m

$280

New WindsorPortland

SWF - PDX

SWFPDX

New Windsor Stewart

Sat 6/27

6:45 pm-1:48 pm

2 stops22h 03m

$344

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/2

Sorted by cheapest first
  • Most accurate provider: When it comes to deals on New Windsor-Portland flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on New Windsor-Portland flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from New Windsor-Portland flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Portland flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New Windsor-Portland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Stewart to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Stewart with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from New Windsor to Portland

What is the cheapest month to book a flight from New Windsor to Portland?

Currently, March is the cheapest month in which you can book a flight from New Windsor to Portland (average of $168). Flying from New Windsor to Portland in November is currently the most expensive (average of $261). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Stewart to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find deals for flights from Stewart to Portland that include hotel bookings?

    Yes. In addition to deals on Stewart to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Portland.

  • Can I find deals for business class flights from Stewart to Portland?

    Yes. Cheapflights offers flight deals from Stewart to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New Windsor to Portland?

    Currently, March is the cheapest month in which you can book a flight from New Windsor to Portland (average of $168). Flying from New Windsor to Portland in November is currently the most expensive (average of $261). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
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Long Beach
McMinnville
Tigard
The Dalles
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